He can be talking about 2 things.
1) Add him to transfer list and let your director of football handle the transfer. Usually I find this cumbersome and you normally have to overpay to get the players you want while the DoF will very rarely be willing the pay the price. Hate using this.
2) You make the transfer bid and let your DoF handle contract negotiations. Under staff responsibilities you can set your Director of Football to handle incoming transfer contract negotiations. Personally I like using this alot as your DoF will try and get the best contract for the club whereas whenever you negotiate the contract the agent usually reams you a new one. Your DoF will need high Motivation, Determination, Man Management, Reputation, and Good JPA/JCA.
From what is sounds like you're having trouble getting him to even negotiate a contract. If you DoF's rep is high enough should go with #2